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Merck

419796

Sigma-Aldrich

6-Hydroxyflavanon

99%

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About This Item

Empirische Formel (Hill-System):
C15H12O3
CAS-Nummer:
Molekulargewicht:
240.25
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Assay

99%

Form

solid

mp (Schmelzpunkt)

220-222 °C (dec.) (lit.)

SMILES String

Oc1ccc2OC(CC(=O)c2c1)c3ccccc3

InChI

1S/C15H12O3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-8,15-16H,9H2

InChIKey

XYHWPQUEOOBIOW-UHFFFAOYSA-N

Angaben zum Gen

rat ... Ar(24208)

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Allgemeine Beschreibung

6-Hydroxyflavanone is a flavonoid. Its biotransformation by Aspergillus niger strains have been described. Crystal structure of S and R enanti­omers of 6-hydroxyflavanone has been reported to have four crystallographic sites of the unit cell in an approximate 3:1/1:3 ratio. It was identified as a metabolite of flavnone on incubation with rat liver microsomes by positive ion electrospray LC/MS analysis.

Anwendung

6-Hydroxyflavanone (6-HF) has been used for the enantiomeric separation of flavonoids using polysaccharide-based chiral stationary phases by nano-liquid chromatography (nano-LC). Racemic 6-HF may be used in the synthesis of 6-propionoxy-flavanone (6-PF). 6-HF may be employed as synthetic flavone to investigate the mechanism of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) induced cytotoxic and apoptotic effects in HeLa cancer cells.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Disordered 6-hydroxyflavanone.
Bialonska A, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(2), 430-431 (2007)
Ewelina Szliszka et al.
Molecules (Basel, Switzerland), 17(10), 11693-11711 (2012-10-03)
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is considered as the most promising anticancer agent in the TNF superfamily because of its selective cytotoxicity against tumor cells versus normal primary cells. However, as more tumor cells are reported to be resistant
Dejan Nikolic et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(4), 387-397 (2004-03-25)
Flavonoids represent a diverse group of natural pigments widely distributed in the plant kingdom and are an important component of human diet due to their high content in fruits and vegetables. Since many flavonoids have been shown to be potent
Microbial transformations of flavanone and 6-hydroxyflavanone by Aspergillus niger strains.
Kostrzewa-Suslow E, et al.
Journal of Molecular Catalysis. B, Enzymatic, 39(1), 18-23 (2006)
Tomohide Uno et al.
Biopharmaceutics & drug disposition, 36(8), 552-563 (2015-07-30)
CYP2A6 is a major hepatic member of the cytochrome P450 family in humans. Much variation in CYP2A6 levels and activity can be attributed to genetic polymorphisms of this gene. CYP2A6*25 comprises an amino acid substitution, F118L. To clarify the effect

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